HMX (1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane) is the most powerful non-atomic explosive in military use, but widespread use of this explosive has been limited by its excessive cost. Although HMX was first discovered in 1941, the only known process for its manufacture comprises nitrolysis of hexamethylenetetramine with a mixture of nitric acid and acetic anhydride, essentially as described by Castorina and coworkers (J.A.C.S., 82, 1617 (1960)). This process has deficiencies, notably poor yield of HMX on a methylene basis and high consumption of acetic anhydride.
It has been proposed to produce HMX by nitrolysis of TAT (1,3,5,7-tetraacetyl-1,3,5,7-tetraazacyclooctane). However, such attempts have been unsuccessful (G. C. Bassler, "The Chemistry of Cyclonite," PhD Thesis 1943, Pennsylvania State College, pages 179-180). These attempts have included treatment of TAT with (a) 100% nitric acid at temperature ranging from -30.degree.C. to -50.degree.C., (b) mixtures of ammonium nitrate +acetic anhydride at 70.degree.C., and (c) mixtures of 100% nitric acid and acetic anhydride at temperatures from 0.degree.C. to 25.degree.C. The first two procedures gave no water-insoluble products, while the last produced a water-insoluble compound, which was not HMX.